Methanol → HCID 45121652, compound

Participants

Reaction Conditions

Reaction Steps

Butan-2-one (20 g, 277 mmol) and 200 mL MeOH were charged into a 1 L round bottom flask. A small amount of Br2 (5 mL) was added to the flask to initiate the reaction. The reaction initiated, and the mixture was stirred at 20° C. until the orange color disappeared. The reaction flask was immersed in an ice-water bath and Br2 was slowly added through an addition funnel. A total of 6 to 8 g (554 mmol) of Br2 was added. Thiourea (21 g, 278 mmol) was then added in portions to the reaction flask. After addition, the reaction mixture was heated at reflux for 2 hours. After the solvent was evaporated, the remaining residue was mixed with saturated sodium bicarbonate. The resulting mixture was extracted with EtOAc, and the combined organic layers were washed with brine and dried over sodium sulfate. The product 4-(1-methoxyethyl)-thiazol-2-amine (22 g, yield=50%) was obtained and used in the next step without further purification. LCMS (API-ES) m/z (%) 159.2 (100%, M++H).

Provenance & Evidence